


When Will I Learn

by The_Onyx_Moon



Series: From the Outside [10]
Category: Supernatural
Genre: Bondage, F/M, Light Bondage
Language: English
Status: Completed
Published: 2019-06-04
Updated: 2019-06-04
Packaged: 2020-04-05 04:57:12
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,323
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19041574
Author URL: https://archiveofourown.org/users/The_Onyx_Moon/pseuds/The_Onyx_Moon
Summary: Dean Winchester is trouble.  Why oh why can’t you stay out of trouble?!





	When Will I Learn

**Author's Note:**

> another small drabble for our Winchester boys. I’m just getting a feel for writing them at the moment so I will be putting out more fleshed out pieces with them soon!

“Oh no, you don’t!”  You huff, mostly to yourself, as you jog up to the two men in perfectly fitting suits. 

“Excuse me, ma’am.”  The shorter of the two says and you grind your teeth at the overconfident smile on his face.  “But this is police business, we’re going to have to ask you to clear the premises.”

“I’m sorry, Agent-”  You look at the fake I.D. he flashes you and grimace.  “Normous, but this is  _my_  crime scene.”  You flash your own I.D., trying your best not to look smug.  It doesn’t work.  “And I’ve already questioned this poor woman.  No need to make her go through all the gory details again.”  The choice of words isn’t great and you immediately feel a pang of guilt, apologizing for your crassness and for her loss.  The woman merely blows her nose comically loud into her handkerchief and returns inside with the  _actual_ cops.

“What the hell, Y/L/N?”  Dean whispers, hauling you away by your elbow.  Same merely rolls his eyes and walks inside to study what exactly it is you’re dealing with here.  “You’re gonna blow our cover!”

“What’s the matter, Agent  _Normous_  - really inconspicuous, by the way - scared I’ll solve it first?”  He scoffs, pretty eyes rolling.  If he wasn’t so damn smug, you might even comment on how gorgeous his smirk is and the way it lights up his face - _ **no**_.

“With Sammy setting his brains to this case?  I highly doubt it.”  You grumble at the confidence in his tone, but you aren’t going to give up so easily.

“C’mon, Dean!  You can’t steal this hunt from me!  I got here first!”  He cocks an eyebrow, smirk growing ever wider as you all but stomp your foot in protest.

“Aww, didn’t realize we were following playground rules here, angel.”  He winks.  Your teeth grind.  That nickname always did things to you.  “I mean, I know you’re a kid and all, but-”

“I’m literally two years younger than you.  Get off your high horse.”

“But it’s so nice up here!”  He says, all grandiose and dramatic with arms cast wide and voice bellowing.  Patience worn thin, you take a deep breath before shoving past him and into the house.  He follows behind you, whispered warnings to not play around, but you’re ignoring him as best you can.  “Fine.”  He says finally, pulling you into a vacant room.  “How about we make this interesting?”

You cock a brow as if to say ‘ _I’m listening_.’  Ever sure of himself, Dean continues.

“Let’s make a little bet of this, shall we?”   _And so it begins…_   “If you can solve and end this before we can, then we’ll let you have a head start and first dibs on hunts for the next…let’s say 4 months?”  Tempting, sure.  But you knew better than to blindly take a gamble with the likes of him.

“What’s the catch?”  Ah.  There’s his infamous smirk.  Your heart flutters a bit at the site and you have to bite the insides of your cheeks to keep from grinning back.

“No catch.”  He shrugs.  “But if we win - you have to let me buy you a drink.”

His hand meets the halfway point between you - calloused from countless weapons and fights - confident that you’re going to seal the deal.  When it’s obvious you aren’t going to take the deal, he looms closer, voice dropping several octaves and eyes alight with mischief.

“C’mon, angel.  You know how much you like drinking with me.  And what usually comes after…”  He’s so close, fingers inches from your skin.  Maybe this could be quick.  A wham-bam-thank-you-ma’am deal and you could be on your way…

“Fine.”  You huff, shaking his hand with as much spite as you can muster and as a means to shove him away.  His proximity is too much to think straight.  “You’re on, Winchester.  Just don’t be a sore loser.”  A deep chuckle, one that reaches all the way down to your toes.

“Wouldn’t dream of it, sweetheart.”

* * *

The bet wasn’t fair.

Really, not fair at all.

Two against one?

Scratch that.

Two giant, crime-fighting Adonises against one  ~~little girl~~   _woman_ who is trying and failing to cover as much ground as they are in the same amount of time?

You groan to yourself, resisting the urge to wack your head against the steering wheel of the car.  Your map was laid open on it, circles and figures drawn all over as you narrowed down the possible suspects and/or causes of the mysterious deaths around town.

Finally, the pieces all fell into place and you had high tailed it to the local graveyard with a shovel, salt, and gas in tow.

Of course, when you pull up the first thing your headlights shine on are the Winchesters - already setting fire to the remains of the pissed off foreman who was seeking revenge on all of the workers who banned together to get him fired.

“Damn it!”  You cry, wadding up the map and throwing it into your passenger seat.  “Mother fucking shit on a stick - pisser!”

Your curses really don’t make sense at this point - just a stringing together of words to keep what you really thought at bay.

Dean Winchester had outsmarted you again - or, more likely, Sam had - and now the fucker owed you a drink.  That, and he was so deliciously smug after he won these little bets.  You’d never tell him it was times like that when you wanted him most.

“Heyya, princess.”  The man in question greets, sidling up alongside your open car window.  Inside, you’re crossing your arms, pouting like a child, but damn it.  You couldn’t care less who saw you.  You were pissed, and you were going to let him know it.

He merely leans on your open window, chin tucked against his arms as he pouts his lower lip comically and bats those green eyes at you.  

“Aww, c’mon, Y/L/N.  No hard feelings, huh?  Sammy and I are just better hunters than you!”

“There’s also  _two_ of you, asshole.”  Your glare boarders on lethal.

“Maybe I just really wanted to buy you that drink, Y/N…”  His eyes flash, that sinful tongue sweeping over full lips, and you’re powerless to the way he plays you so well.  “You know how much I love drinking with you.”  You hum in agreement, unable to keep your own eyes from following the movement of his mouth.

“You love the drinking?”  You challenge, brow cocked.  “Or what comes after it?”

His smirk is all-telling and sends a shiver straight down your spine.

“Fine,” You level, unlocking your passenger side door and nodding him over.  “ _One_  drink.”

* * *

Your limbs ache pleasantly as you wake, a small stretch causing several satisfying pops from various joints.  The night before had been amazing.  Dean knew just what to do with those ringed fingers, the cocksure son of a bitch able to get you off multiple times before the main event.

You smirk at the thought, Dean always was good with his hands.  Maybe it was a good thing he had won the bet after all… you got a free drink out of it, a great lay,  _and_ you didn’t have to touch a nasty old corpse.

“You really know how to treat a lady, Winchester.”  You laugh, eyes opening for the first time in the bright morning sun.  After a moment of letting your eyes adjust, your heart stops dead in your chest and the smile melts from your face.

There, where Dean had been the night before, was a note and just beyond that,  _juuust_ out of reach - were the keys to your handcuffs.

“Damn it!”  You cry, free fist slamming down on the bedside table.  You ignore the dull throbbing that results from this.  “When will I learn?!”

> **_Hey angel,_ **
> 
> **_Thanks for the drinks.  And what came after._ **
> 
> **_Til next time._ **
> 
> **_\- Dean_ **


End file.
